Cephalosporin C
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Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Cephalosporin C
- DrugBank Accession Number
- DB03313
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 415.418
Monoisotopic: 415.104935353 - Chemical Formula
- C16H21N3O8S
- Synonyms
- 7-(5-Amino-5-carboxyvaleramido)cephalosporanic acid
- Cephalosporin C
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APenicillin-binding protein 1b inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APeptidoglycan synthase FtsI antagonistEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2a inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae UD-alanyl-D-alanine carboxypeptidase Not Available Streptomyces sp. (strain R61) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Cephalosporin C. Amifampridine The risk or severity of seizure can be increased when Cephalosporin C is combined with Amifampridine. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Cephalosporin C. Brexanolone The therapeutic efficacy of Brexanolone can be decreased when used in combination with Cephalosporin C. Brivaracetam The therapeutic efficacy of Brivaracetam can be decreased when used in combination with Cephalosporin C. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- D-alpha-amino acids / Tricarboxylic acids and derivatives / Cephems / 1,3-thiazines / Tertiary carboxylic acid amides / Amino acids / Azetidines / Carboxylic acid esters / Thiohemiaminal derivatives / Propargyl-type 1,3-dipolar organic compounds show 9 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid / Amine / Amino acid / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboximidic acid show 25 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:15776) / Cephems (C00916)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3XIY7HJT5L
- CAS number
- 61-24-5
- InChI Key
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N
- InChI
- InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
- IUPAC Name
- (6R,7R)-3-[(acetyloxy)methyl]-7-[(5R)-5-amino-5-carboxypentanamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CCC[C@@H](N)C(O)=O)C(O)=O
References
- Synthesis Reference
Chun-Lung Hsieh, "Process for preparing alkali salts of cephalosporin C." U.S. Patent US5403929, issued May, 1972.
US5403929- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0060450
- KEGG Compound
- C00916
- PubChem Compound
- 65536
- PubChem Substance
- 46505733
- ChemSpider
- 58980
- ChEBI
- 15776
- ChEMBL
- CHEMBL482858
- ZINC
- ZINC000003977881
- PDBe Ligand
- CSC
- Wikipedia
- Cephalosporin_C
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source logP -4.4 Chemaxon pKa (Strongest Acidic) 1.83 Chemaxon pKa (Strongest Basic) 9.22 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 176.33 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 95.43 m3·mol-1 Chemaxon Polarizability 39.7 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9983 Blood Brain Barrier - 0.9961 Caco-2 permeable - 0.7586 P-glycoprotein substrate Substrate 0.8668 P-glycoprotein inhibitor I Non-inhibitor 0.8709 P-glycoprotein inhibitor II Non-inhibitor 0.9931 Renal organic cation transporter Non-inhibitor 0.9164 CYP450 2C9 substrate Non-substrate 0.8183 CYP450 2D6 substrate Non-substrate 0.8243 CYP450 3A4 substrate Non-substrate 0.5068 CYP450 1A2 substrate Non-inhibitor 0.7811 CYP450 2C9 inhibitor Non-inhibitor 0.8224 CYP450 2D6 inhibitor Non-inhibitor 0.9025 CYP450 2C19 inhibitor Non-inhibitor 0.7893 CYP450 3A4 inhibitor Non-inhibitor 0.8812 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8764 Ames test Non AMES toxic 0.6963 Carcinogenicity Non-carcinogens 0.9617 Biodegradation Not ready biodegradable 0.5154 Rat acute toxicity 1.9527 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.981 hERG inhibition (predictor II) Non-inhibitor 0.8359
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9328000000-51dcafd0526ede8e8796 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-08fs-0029100000-f52b60551a019fd45b0e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001d-1619000000-5b99f8124448ac90654d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052b-0149000000-e967a088831014361d42 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0aor-6789000000-588d337a41c41cfe2c16 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0r00-1956100000-b7f4011d82d9b159902e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-9141000000-32a1265d2c870859b338 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 207.4313988 predictedDarkChem Lite v0.1.0 [M-H]- 209.1052988 predictedDarkChem Lite v0.1.0 [M-H]- 188.64894 predictedDeepCCS 1.0 (2019) [M+H]+ 204.7674988 predictedDarkChem Lite v0.1.0 [M+H]+ 208.5192988 predictedDarkChem Lite v0.1.0 [M+H]+ 191.04451 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.0976988 predictedDarkChem Lite v0.1.0 [M+Na]+ 208.5462988 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.95705 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsPenicillin-binding protein 1b
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- acyltransferase activity
- Gene Name
- pbp1b
- Uniprot ID
- Q7CRA4
- Uniprot Name
- Penicillin-binding protein 1b
- Molecular Weight
- 89479.92 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
2. DetailsPeptidoglycan synthase FtsI
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Essential cell division protein that catalyzes cross-linking of the peptidoglycan cell wall at the division septum (PubMed:1103132, PubMed:3531167, PubMed:6450748, PubMed:7030331, PubMed:9614966). Required for localization of FtsN (PubMed:9282742).
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsPenicillin-binding protein 1A
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation.
- Specific Function
- penicillin binding
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
4. DetailsPenicillin-binding protein 2B
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- A transpeptidase that forms peptide cross-links between adjacent glycan strands in cell wall peptidoglycan (PG). Part of the elongasome machinery that synthesizes peripheral PG.
- Specific Function
- penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
5. DetailsPenicillin-binding protein 2a
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan (PG) from the lipid intermediates (By similarity). Binds dansylated lipid II and catalyzes the polymerization of glycan chains (PubMed:12867450, PubMed:22487093). Hydrolyzes S2d (N-benzoyl-D-alanylmercaptoacetic acid) molecule, a synthetic thiolester analog of cell wall stem peptide (PubMed:10217767, PubMed:22487093). Active against bocillin, a fluorescent penicillin. No transpeptidase activity with non-fluorescent lysine-containing lipid II as substrate (PubMed:22487093).
- Specific Function
- acyltransferase activity
- Gene Name
- pbp2a
- Uniprot ID
- Q8DNB6
- Uniprot Name
- Penicillin-binding protein 2a
- Molecular Weight
- 80797.94 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
6. DetailsPenicillin-binding protein 3
- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- Gene Name
- pbp3
- Uniprot ID
- Q75Y35
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
7. DetailsD-alanyl-D-alanine carboxypeptidase
- Kind
- Protein
- Organism
- Streptomyces sp. (strain R61)
- Pharmacological action
- Unknown
- General Function
- Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e. a D-alanyl-D-alanine-terminated peptide), it becomes immobilized in the form of a long-lived, serine-ester-linked acyl enzyme and thus behave as penicillin-binding protein (PBP).
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- Gene Name
- Not Available
- Uniprot ID
- P15555
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase
- Molecular Weight
- 42916.725 Da
References
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22